Acetic Acid → HCID 59556687, compound

HRID 1172971Notes

Reaction equation

HRID 1172971 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([C:14]3[CH:15]=[CH:16][C:17]([O:22][CH:23]([CH3:25])[CH3:24])=[C:18]([CH:21]=3)[C:19]#[N:20])[N:10]=2)=[CH:5][CH:4]=1)=O.[NH:26]1[CH2:29][CH:28]([C:30]([OH:32])=[O:31])[CH2:27]1.C(O)(=O)C.C([BH3-])#N>CO.ClCCCl>[C:19]([C:18]1[CH:21]=[C:14]([C:11]2[N:10]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([CH2:1][N:26]4[CH2:29][CH:28]([C:30]([OH:32])=[O:31])[CH2:27]4)=[CH:8][CH:7]=3)[O:13][N:12]=2)[CH:15]=[CH:16][C:17]=1[O:22][CH:23]([CH3:25])[CH3:24])#[N:20]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 931923-azetidinecarboxylic AcidHCID 498716Cyano-borohydrideHCID 59556702HCID 59556702, compound

Product 1

HCID 59556687HCID 59556687, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

5-(5-(4-formylphenyl)-1,2,4-oxadiazol-3-yl)-2-isopropoxybenzonitrile (0.077 g, 0.231 mmol) and azetidine-3-carboxylic acid (0.028 g, 0.277 mmol) were combined in methanol (11.55 ml) and DCE (11.55 ml) in a sealed vial. Acetic acid (0.066 ml, 1.155 mmol) was added. The reaction mixture was stirred at ambient temperature for 2 hr. MP-cyanoborohydride (0.265 g, 0.570 mmol) was added and the reaction stirred for about 24 h. The solution was filtered, the solid was washed with methylene chloride and methanol, and the filtrate was concentrated to afford a white solid, which was recrystallized by methanol (5 mL) to give 1-(4-(3-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-5-yl)benzyl)azetidine-3-carboxylic acid (0.025 g, 0.060 mmol, 25.9% yield) as white solid: LC/MS (Table 1, Method a) Rt=2.10 min.; MS m/z: 420.26 (M+H)+. 1H NMR (400 MHz, Solvent d-DMSO) ppm 8.35-8.28 (m, 2H), 8.17-8.11 (d, J=8.00 Hz, 2H), 7.56-7.50 (m, 8.69 Hz, 3H), 4.98-4.89 (m, 1H), 3.68 (s, 2H), 3.43 (s, 2H), 3.25-3.23 (m, 3H), 1.38 (d, J=6.03 Hz, 6H).

Workup

  1. stirringthe reaction stirred for about 24 h
  2. filtrationThe solution was filtered
  3. washthe solid was washed with methylene chloride and methanol
  4. concentrationthe filtrate was concentrated
  5. customto afford a white solid, which
  6. customwas recrystallized by methanol (5 mL)

Sources & evidence

ORD record
ord-33c2e45e138340bd9a911447d9704bcb
Source dataset
uspto-grants-2010_11
Patent number
US07834039B2

Reaction notes

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